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Sodium Methoxide → 2-Methyl-2-(3,3,3-trifluoro-propylsulfanyl)-propionic acid ethyl ester

HRID 386920
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HRID 386920 반응식
[CH2:1]([O:3][C:4](=[O:12])[C:5]([S:8][C:9](=O)[CH3:10])([CH3:7])[CH3:6])[CH3:2].[F:13][C:14]([F:29])([F:28])CCOS(C1C=CC(C)=CC=1)(=O)=O.C[O-].[Na+]>C(O)C>[CH2:1]([O:3][C:4](=[O:12])[C:5]([CH3:7])([S:8][CH2:9][CH2:10][C:14]([F:29])([F:28])[F:13])[CH3:6])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10942334Sodium MethoxideHCID 126353403,3,3-Trifluoroprop-1-yl toluene-4-sulphonateHCID 57937863Ethyl 2-(acetylthio)-2-methylpropanoate

생성물 1

HCID 592532102-Methyl-2-(3,3,3-trifluoro-propylsulfanyl)-propionic acid ethyl ester수율 82.6%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 2-acetylsulfanyl-2-methyl-propionic acid ethyl ester (1.7 g, 8.72 mmol), toluene-4-sulfonic acid 3,3,3-trifluoro-propyl ester (2.3 g, 8.72 mmol) and sodium methoxide (1.9 g, 34.9 mmol) in ethanol (13 mL) are heated to 130° C. in a sealed tube for 4 h. The reaction is cooled to room temperature and concentrated under reduced pressure. The residue is diluted with DCM and washed with saturated aqueous NaHCO3 solution and brine. The organic layer is dried (Na2SO4), filtered and the filtrate concentrated under reduced pressure to afford 1.76 g of title compound as a brown solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.28 (3H, t, J=7 Hz), 1.51 (3H, s), 2.26-2.42 (2H, m), 2.76-2.85 (2H, m), 4.18 (2H, q, J=6.96 Hz)

후처리

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue is diluted with DCM
  3. washwashed with saturated aqueous NaHCO3 solution and brine
  4. dry with materialThe organic layer is dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-8fe83ec184a2435e83ccf1961143b081
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08372874B2

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